Director Regional Sales/ RVP

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Director Regional Sales / RVP based in Canada.

This leadership role is responsible for driving sales performance across a significant Canadian customer and prospect portfolio. You will set regional strategy, lead execution, and guide a team of sales professionals toward quarterly and annual revenue objectives. The position combines strategic planning, sales leadership, pipeline management, customer engagement, and team development. You will build executive-level relationships and identify opportunities to expand existing accounts through cross-selling, upselling, and demand creation. Working in a consultative software-sales environment, you will partner with customers, sales teams, and senior leadership to accelerate growth. This is a fully remote, full-time opportunity with approximately 50% travel required.

• Develop and execute the regional sales strategy and vision in alignment with senior leadership, company strategy, and annual business plans.
• Lead, manage, motivate, and develop multiple sales professionals, ensuring teams consistently meet or exceed assigned sales quotas and performance expectations.
• Own the regional sales pipeline and drive opportunities through the sales process from prospecting and qualification through negotiation and closure.
• Identify, prospect, qualify, and close new business opportunities while supporting Account Executives in complex sales negotiations.
• Build and maintain strategic relationships with customers and prospects, particularly key and executive-level accounts, to maximize business opportunities.
• Establish clear objectives, assign responsibilities, and maintain accountability across virtual sales teams.
• Forecast sales accurately and provide regular weekly updates and detailed pipeline insights to sales leadership using agreed tools and processes.
• Deliver quarterly and annual sales revenue targets while maintaining focus on core performance metrics.
• Mentor, coach, and develop sales professionals, supporting their growth and strengthening overall team capabilities.
• Oversee sales-team hiring, development, and performance management in line with organizational needs.
• Ensure sales processes and methodologies are clearly understood, consistently followed, and effectively applied across the region.
• Develop market and segment strategies and provide structured reporting on key opportunities, emerging markets, and growth initiatives.
• Work directly with sales professionals to develop territory plans focused on demand creation, account penetration, cross-selling, and upselling.
• Participate in sales calls and product or solution demonstrations when appropriate, providing hands-on sales leadership and coaching.
• Serve as a role model for organizational culture, collaboration, accountability, and customer focus.

Requirements

• Bachelor’s degree required; MBA, MA, or equivalent professional experience is preferred.
• 12+ years of overall sales experience, including at least 8 years in sales leadership within the software or related technology industry.
• Proven experience selling software solutions and managing complex B2B sales cycles.
• Demonstrated leadership experience with a strong record of performance management, coaching, and professional team development.
• Ability to operate effectively at both strategic and operational levels, translating business strategy into measurable sales execution.
• Established relationships and contacts with potential customers and business stakeholders.
• Strong consultative selling capabilities and exceptional interpersonal skills, particularly when engaging executive-level customers and partners.
• Proven track record of generating sales in new product or new market environments.
• Experience with sales methodologies, sales funnel management, and CRM platforms, preferably Salesforce.
• Exceptional written, verbal, presentation, and communication skills across a wide range of audiences.
• Proven ability to interact effectively with C-level and other senior management stakeholders.
• Strong team-management, customer-facing, negotiation, and relationship-building capabilities.
• Demonstrated ability to identify, develop, and retain high-performing sales talent.
• Collaborative and results-oriented leadership style with the ability to build a strong team environment.
• Willingness and ability to travel approximately 50% of the time.
• Successful completion of applicable background screening processes may be required, including employment, education, criminal, sanctions, and other checks as permitted by applicable regulations.

Benefits

• Full-time, fully remote opportunity based in Canada.
• Competitive compensation aligned with senior sales leadership responsibilities.
• Opportunity to lead regional sales strategy and influence significant customer and prospect relationships.
• High level of visibility with senior leadership and executive-level customers and partners.
• Opportunity to manage, mentor, and develop experienced sales professionals.
• Exposure to strategic software sales, consultative selling, new-market development, cross-selling, and upselling.
• Opportunity to contribute directly to regional growth and quarterly and annual revenue objectives.
• Approximately 50% business travel, providing opportunities for customer and partner engagement.
• Collaborative, team-oriented environment focused on professional development, accountability, and customer relationships.